Yarn having the twist set therein with an unctuous solid



I Patented Apr. 8, 1947 UNITED STAT Es PATENT. OFFICE YARN HAVING THETWIST SET THEBEIN WITH AN UNCTUOUS SOLID Kenneth R; Brown, WestChestenlfa ass'lgnoigby mesne assignments, to American ViscoseCorporation, a corporation of Delaware 4N0 Drawing. Application April24, 1943, I Serial No. 484,493

16 Claims. 1

'apply and is readily removed from the filamentary material when it is-no longer needed, which imparts pliability, softness and lubricity tothe treated filamentary material, and which s capable of setting thetwist and maintaining its uniformity, particularly in highly twistedyarns,

and at the same time is free of any tendency to be stripped from thefilamentary material while it is being subjected to the severest flexingand rubbing action during the course of textile'processing, such as inknitting or spinning.

It has been found that these results can be satisfactorily fulfilled bythe application, to the yarns and the like, of unctuous to waxy solidshaving melting points ranging between 30 C. and about 70 C. or highercomprising higher fatty acid esters of ethers of polyols having at leastthree hydroxyl groups formed by condensation of such a polyol with anolefine oxide preferably having no more than 3 carbon atoms. The termpolyol is meant to include only polyhydric alcohols and carbohydrates.These compounds may be prepared, by' way of illustration, by firstcondensing in the presence or absence of water an olefine oxide, such asethylene oxide or propylene oxide, with one or more of such polyhydricalcohols as glycerol, diglycerol, pentaerythritol, erythritol, sorbitol,sorbitan, mannitol, inannitan,

dulcitol, dulcitan or of related polyols including the carbohydrates,such as glucose and other sugars, and then subjecting the condensationproduct to esterification with a higher saturated fatty acid having atleast 16 carbon atoms in a straight chain or a mixture of .one or moreof such higher fatty acids with a relatively small proportion of one ormore higher unsaturated fatty acids. The maximum proportion ofunsaturated fatty acid that may be used depends upon the particularacid, the nature and amount of saturated fatty acid used and the natureand amount of alkylene oxide combined in the molecule. Generally atleast two thirds or moreof the acyl radicals in the final compound mustbe saturated. The esterification contemplated by the invention rangesfrom about 70% of the calculated free hydroxyl groups in the ether up tocomplete esterification thereof. The fatty acids may be those obtainedby the saponification of.

palmitin, stearin and the like or of animal and vegetable oils, suchasfish oils, olive oils, lards,

or fractions thereof having the desired long carbon chain and thesubsequent hydrogenation of such of the above-mentioned fatty acids asare highly unsaturated to complete saturation or at least to attain theratio specified above between the saturated and unsaturated acids. Theesters of the condensation products obtained from substantially purecompounds as well as those "obtained from commercial grades of theseveral compounds have both been found to function satisfactorily. Inaddition, a mixture of two or more of the pure polyhydric alcohols maybe reacted with a mixture of two or more olefine oxides.

The proportion of alkylene oxide that is present in the compounds may bevaried considerably provided there are not so many olefine oxide unitsper mol of the compound as to make it of too low a melting point. Thepermissible proportion of olefine oxide depends upon the particularoxide as well as 'the molar proportion of the ester radicals presenttherein and the particular ester radical and especially upon the ratiobetween saturated and unsaturated acids. For example, sorbitol cantolerate up to about 20 mols of oxyethylene units per mol if the productis then completely esterified with stearic acid, whereas only about onethird this number of oxypropylene groups is permissible; Where acorresponding palmitic or oleic ester compound is involved, the upperlimit of oxyolefine groups is correspondingly reduced.

The compounds contemplated by this invention are unctuous and waxysolids having melting. points between 30 C. to about 70 C. Dependingupon the ambient temperature where the treated yarns areto be subjectedto textile operations, a compound having a higher or a lower meltingpoint (or titer) is to be preferred. For a given ambient temperature, acompound should be selected which remains solid at that tem-.

not have such a high melting point that exces sively high temperatures,which might harm the textile materialsare required in the scouring bathto effect melting and thereby hasten emulsification. Those compoundshaving lower meltin points in the neighborhood of about 35 C. to 45 C,render exceptional satisfaction under normal 3 conditions of service.The following table sets forth illustrative examples, giving the numberof mols of olefine oxide condensed with one mol of the polyhydricalcohol and the number of mols of acid or mixed acids with which thecondensa- -cellulose from viscose or cuprammonium solutions or tofilamentary materials of organic derivatives 5 of cellulose, such ascellulose acetate, of nylon, tion product is estenfied: casein, and alsothe filamentary material derived No. Polyhydrlc Alcohol Mols of OlefineOxide Mcis of Fatty Acid 4 ethylene oxide 6 stearic. 6 ethylene oxideDo.

(in D0. do 6 mixed acids, 75% stearic, balance chiefly almltlc. d 6hydrogenated fatty acids derived from fish oil. do 6 hydr ted fattyacids from soya bean oil. dn 6 hydrogenated fatty acids from cottonseedoil.

6 pslmitic. do 1 l oleic mixed with 6 hydrogenated fatty acids from soyabeen oil. do 1 lauric mixed with hydrogenated fatty acids from wttonseedoil. ..do 1 ablctic mixed with 5 hydrogenated fatty acids from fish oil.

8 ethylene oxide 6 stearlc. l2 ethylene oxide Do. do 6 hydrogenatedfatty acids from soya bean oil.

mixture of 3 ethylene Do.

3 propylene oxide. --.-do

oxide and 17..... .do-.. 3 propylene oxide 18 {sorbitol 3 ethy ene oxidemannitol 3 prop lene oxide--- 19....- pentaerythritol 4 ethy cncoxide..--.

20.. diglycerol. do

21 .do 6 ethylene oxide 3 ethylene oxide... 6 ethylene oxide 5 ethyleneoxide 4 ethylene oxide ..I 6 ethylene oxide 6 stearic. .6 hydrogenatedfatty acids from soya bean oil.

4 stearic.

I In No. 18 of the table the ethylene oxide condensation product ofsorbitol was formed separately and then mixed with an equal proportionof the propylene oxide condensation product of mannitol after which themixture was estenlied.

These compounds may be applied singly or as a mixture to the filamentarymaterial either in molten condition, in the form of a solution in asuitable organic solvent or in the form of a dispersion or emulsion inwater. Where it is applied in the form of an emulsion, the temperatureof the emulsion is preferably above the melting point of the compound.The filamentary material may be sprayed with or immersed in the solutionof the compound. Where application is to be made to yarns and the likeof continuous character, application may be made by directing them overa conventional form of roller running in a trough supplied with thesolution or dispersion as the yarn runs from one package to another.Alternatively, a wound package of the yarn may be immersed in thedispersion or solution for a sufficient time to permit completepenetration. Excess solution is removed in any suitable manner, such asby a centrifugal hydroextractor and then dried. The treated filamentarymaterial may then be stored, if desired,-under controlled humidityconditions until used in subsequent textlle processing. The amount ofthe compound to be applied to the filamentary material depends upon thepurpose for which it is applied and will be more fully explainedhereinafter.

The compounds may be applied in conjunction with the application ofother treating agents, such as antistatic agents, auxiliary softeners,lubricants, oils, or sizing agents. The auxiliary substances may beapplied before or after the application of the compounds of theinvention or they may be mixed and applied together in molten condition,or in the form of a dispersion, solution or emulsion.

The compounds of the invention are applicable to both natural andsynthetic fibers or filaments. For example, they may be applied tofibers, filaments or yarns of cotton, wool, linen and silk, particularlysilk which has been degummed, and other materials of natural origin.They are how- 'These compounds may be applied to highly twisted yarns ofrayon, such as to a denier yarn having above 25 turns per inch, toreduce their harshness and stifiness and to set the twist therein. Forthe purpose of lubricating, imparting flexibility to and setting thetwist in such yarn, to prepare them for subsequent textile processing,such as for the knitting of full fashioned hosiery or for weaving voileor crepe fabrics, the impregnation is controlled to incorporate withinthe yarn between about 8 to 11% of its weight of such compounds,preferably about 10%. For the application of this amount of thecompound, a 50% concentration of such compound in an organic solvent,such as Stoddard solvent or other petroleum solvents such as that soldunder the trade-mark Solvesso No. 3, is satisfactory. Alternatively, a10% concentration of the compound is an aqueous dispersion may beemployed. A dispersing agent, such as an alkyl aryl sulfonate, such asthose sold under the trade name'Nekal BX, may be employed to form theaqueous dispersion. During the severe flexing and rubbing action towhich such treated yarns are subjected by the needles of knittingmachines, substantially no stripping occurs and the knitted fabric has afirm but soft hand. After completion of the fabric, the conditioningcompounds may be removed by a simple scouring operation. In thescouring,no harsh detergents I ing compounds is controlled so that from 1 to 5%prove the feel and hand of the fibers and to render them pliantpreparatory to spinning and felting.

v Similarly for the purposes of "lubricating yarns and rendering thempliant preparatory to twisting and winding, the lower percentage of theconditioning compound just specified may be suflicient in which casethere is no point in applying a greater quantity.

For the purpose of lubricating and imparting flexibility to yarn whichare to be woven or braided, it is preferably to impregnate the yarnswith a larger proportion than is used in preparing yarns for knitting.

. While preferred embodiments of the invention have been disclosed, thedescription is intended to be illustrative only, and it is to beunderstood that changes and variations may be made without departingfrom the spirit and scope of the invention as defined by the appendedclaims.

I claim:

1. Twisted textile filamentarymaterial having the twist therein set withan unctuous solid hav ing a melting point between about 30 (Land 70 C.comprising a higher fatty acid ester of an ether condensation product ofa polyol having at least three'hydroxyl groups with an olefine oxide,the hydroxyl groups in the ether condensation product beingsubstantially completely esterified, at least two thirds of the acidradicals in the ester being saturated, and the acid radicals thereinhaving at least 16 carbon atoms in a straight chain.

2. Twisted yarns and the like having the twist therein set with anunctuous solid having a melting point between about 30 C. and 70 C.comprising a higher fatty acid ester of an ether condensation product ofa polyol having at least three hydroxyl groups with an olefine oxidehaving he more than 3 carbon atoms, the hydroxyl groups in the ethercondensation product being substantially completely esterified, at leasttwo thirds of the acid radicals in the ester being saturated, and theacid radicals therein having at least 16 carbonatoms in a straightchain.

3. Twisted yarns comprising fibers or filaments of regenerated cellulosehaving the twist therein set with an unctuous solid having a, meltingpoint between about 30 C. and 70 C. comprising a higher fatty acid esterof an ether condensation product of a polyol having at least threehydroxyl groups with an olefine oxide having no more than 3 carbonatoms, the hydroxyl groups in the ether condensation product beingsubstantial-y completely esterified, at least two thirds of the acidradicals in the ester being saturated, and the acid .radicals thereinhaving at least 16 carbon atoms in a straight chain.

4. Twisted yarns comprising fibers or filaments of regenerated cellulosehaving the twist therein set with an unctuous solid having a meltingpoint between about 30 C. and 70 C. comprising a higher fatty acid esterof a condensation product of a hexitol with an olefine oxide having nomore than 3 carbon atoms, the hydroxyl groups in the condensationproduct being substantially completely esterified, at least two thirdsof the acid radicals in the ester being saturated, and the acid radicalstherein having at least 16 carbon atoms in a straight chain.

5. Twisted yarns and the like having the twist therein set with anunctuous solid having a melting point between about 30 C. and 70 C.comprising a higher saturated fatty acid ester of a condensation productof a hexitol with ethylene oxide, said product being substantiallycompletely esterified,.the fatty acid radicals therein having 'atleast16 carbon atoms in a straight chain.

6. .Twisted yarns'comprising'fibe'rs or' filaments of regeneratedcellulose having the twist therein set with an unctuous solid having amelting point. between about 30 C. and 70 C. comprising a higher fattyacid ester of a condensation product of a hexitol with ethylene oxide,the hydroxyl groups in the condensation product being sub-'1 betweenabout 30 C; and 70 C. comprising a higher fatty acid ester of acondensation product of sorbitol with an olefine oxide having no morethan 3 carbon atoms, the hydroxyl groups in the condensation productbeing substantially com-v pletely esterified, at least two thirds of theacid radicals in the ester being saturated, the acid radicals thereinhaving at least 16 carbon atoms in a straight chain.

8. Twistedsynthetic yarns and the like having the twist therein set withan unctuous solid have ing a melting point between about 30C. and 70 C.comprisin a higher saturated fatty acid ester of a condensation productof sorbitol with ethylene oxide, said product being substantiallycompletely esterified and the acid radicals therein having at least 16carbon atoms in a straight chain.

9. Twisted yarns comprising fibers or filaments of regenerated cellulosehaving the twist therein set with an unctuous solid having a meltingpoint between about 30 C. and 70 C. comprising a higher fatty acid esterof a condensation product of sorbitol with ethylene oxide, the hydroxylgroups in the ether condensation product being substantially completelyesterified, at least two thirds of the acid radicalsin the ester beingsaturated, and the acid radicals therein having at least 16 carbon atomsin a straight chain.

10. Twisted yarns and the like having the twist therein set with anunctuous solid having a melting point between about 30 C. and 70 C.comprising a stearic acid ester of a condensation product of sorbitolwith ethylene oxide, the hydroxyl groups of the condensation productbeing substantially completely esterified. 11. Twisted yarns comprisingfibers or filaments of regenerated cellulose having the twist thereinset with a compound comprising a stearic acid ester of a condensationproduct of about one mol of sorbitol with about six mols of ethyleneoxide, said product being substantially completely esterified.

12. Twisted yarns and the like having the twist therein set with anunctuous solid having a melting point between about 30 C-filld 70 C.comprising a higher fatty acid ester of a condensation productof'mannitol with ethylene oxide, the hydroxyl groups in the ethercondensation product being substantially completely esterified, at least7 two thirds of the acid radicals in the ester being saturated. and theacid radicals having at least 16-carbon atoms in a straight chain.

14. Twisted yarns and the: like having the twist therein set with anunctuous solid having a melting point between about 30 C. and 70 0.comprising a higher fatty acid ester ofva condensation product 01' ahexose with an olefine oxide having no more than 3 carbon atoms, thehydroxyl groups in the ether condensation product being substantiallycompletely esterifled, at least two thirds of the acid radicals in theester being saturated, and the acid radicals therein having at least 16carbon atoms in a straight chain.

15. Twisted yarns and the like having the twist therein set with anunctuous solid having a melting' point between about 30 C. and 70 C.comprising a higher fatty acid ester of a condensation product ofglucose with ethylene oxide, the hydroxyl groups in the ethercondensation product being substantially completely esterified, at

least two thirds of the acid radicals inthe ester being saturated, andthe acid radicals therein having at least 16 carbon atoms in a straightchain. 7

16. Twisted yarns comprising fibers or filaauezrsa 8 1, ments ofregenerated cellulose having the twist therein set with anunctuous-solid having a melting point between about C. and 0. comprisinga stearic acid ester of a condensation product of glucose with about sixmols of ethylene oxide, the hydroayl groups in the ether condensationproduct being substantially completely esterified.

KENNETH R. BROWN.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATIENTS Name Date Schmidt et a1 May 22, 1934 Schoelle'ret al. Aug. 21, 1934 Davis et al. Sept. 29, 1942 Hood June 22, 1937Sherman July 9, 1940 OTHER REFERENCES Pub. Spans and Tweens, AtlasPowder (20.,

Number 25 Wilmington, DeL, Nov 1942.

